Search Results: Liberating The B.o.b. Within

So ya finally decided to become a B.O.B. (Big Old Bottom)? Tired of missing out on all that ass-play everyone’s talkin’ about? Been secretly trippin’ on the exploits of your favorite porn stars? (“Jeez, would ya get a load of that. His hole looks like the Victory Arch in Paris, for god sake.”) And now want a piece of the action for yourself? But wait, there’s a wrinkle, you’re a virgin or worse yet, there’s been an “Exit Only” sign on your poop chute for so long that the mere thought of someone diddlin’ your ass hole makes you blanch and swoon.

Dear Dr. Dick, Help! I want to be a bottom; at least I think I do. My boyfriend’s been begging for my booty big time, (my girlfriend just got herself a strap-on, YIKES!) but I’m just too tight down there and he’s really big (and she thinks turn-about is fair play). Our play time always end the same way, frustration for him (her) and a pain in the ass for me. How do those porno guys and gals do it?

First off, darling, “porno guys,” as you so lovingly refer to them, are professionals (yeah, huh!). And Dr. Dick suggests that a novice butt pirate like you not try that fancy stuff at home before you know the basics.

So listen up, bottom wannabes, pleasurable buggering depends upon on three simple, but important things: 1) The will, 2) Being relaxed and 3) A considerate partner.

First. You gotta really want to get fucked. This may sound elementary, but it’s not. Some of my clients secretly confess that they don’t anyone near their precious tushie, and no amount of pleading and whimpering on the part of their long-suffering partner(s) is gonna change that. For some getting it up the ass is associated with domination not pleasure. Manly men don’t bottom for nobody. (Oh sure Mary, me thinks you doth protest too much.) Others have religious reservations. (If god wanted me to get fucked he would have given me a vagina.) Still others have aesthetic concerns. (Oh no, that’s way too icky and messy.) I can assure you that these boys ain’t never gonna be a bottom no how.

Second. Let’s just say your dyin’ to get fucked, but you’re so intimidated by your top’s one-eyed monster that your quivering asshole is like totally shut down. Chill out! Why not begin your sex play with your partner giving you a relaxing sensual back rub. After awhile he could move on to a little butt play (and I do me play). The object here is pleasure not penetration. Have him tease your asshole with his finger. A tongue works nicely too. (This is called rimming, but you probably already knew that, because you’re not a complete idiot, huh?) A gentle circular motion works best. Have him use his hands to spread your ass cheeks, this will give your top better access to your rosebud and give you a double dose of pleasure. After a while, a lubricated finger can be inserted for a bit of a prostate massage, which is ohhh sooo delicious. When you’re ready to kick it up a notch, have your partner try inserting two fingers or a small dildo. Rhythmic deep breathing will help keep you relaxed. And when you’re all loosened up and ready to become like one of them “porno guys or gals,” you can him plug in the real thing. No more meat substitutes for you. Experiment with different positions. Try sittin’ down on that big old thang, or do it doggie style. Getting laid while on your side with your man comin’ at ya from behind gives you a bit more control over the depth of his thrusting. And of course, there’s also the traditional missionary position; you on your back, legs spread eagle and your pumps pointing to the stars.

Third. Having a big dick doesn’t automatically make a guy a good top. A considerate partner, big dong or not, will happily join you in exploring your asshole. He will concentrate on pleasing you first, because he knows that an investment in your anal pleasure today will reap a harvest of mutual pleasure tomorrow. (Coming soon! Dr. Dick’s tutorial for tops. Don’t miss it.)

Particularly those of you who are living in and around the Emerald City. I have some swell news for ya’ll. I’m scheduled to present one of my most popular workshops at Seattle’s very own woman owned sex emporium, Wild At Heart.

Learn the ins and outs of anal pleasure in this introductory class to backdoor fun. Anal play is a source of curiosity for many, but often surrounded by fear that it’s gonna be painful, or worse- messy. This class will help answer those questions and put those fears to rest.

We’ll cover a wide variety of topics, including:

Anal anatomy

Preparation and hygiene

Lubes, toys, and safer sex

Beginner booty play

All-important warm-up techniques

Anal sex myths and misconceptions

Sex Toy giveaways

and so much more!

We all have one, lets relax and enjoy it!

This workshop is open to all regardless of gender, orientation, or relationship status.

Workshop attendees also get a 15% discount on any store merchandise while they’re at the workshop.

Name: Terre
Gender:
Age: 54
Location: Nashville
I’ve been in a relationship for over 11 years. For sex, I was always the top; occasionally I would bottom. However, now that I have developed erectile dysfunction, I’m lucky to get slightly hard. I cannot penetrate my partner any longer. I’ve tried reversing roles; however, my partner is no good at being a top/aggressive and I’ve found anal sex much too painful including bleeding and profound pain after only attempting to be penetrated by my partner. What can I do to get over this hump? What other things can I try to maintain sexual balance in my relationship?

Get over this “hump,” Terre? You’re such a punster!

Have you tried a cock ring to keep yourself hard enough to bugger your old man? How about dildo play? You still get to be the top and he still gets to be the bottom, it’s just that you’re using a meat substitute instead of your salami.

And what’s all this about you being unable to take it in your bum? I have written extensively about learning to bottom. Check out some of my earlier postings, especially Liberating The B.O.B. Within. Use the site’s search function in the sidebar to your right; type in “Tutorial for a Bottom” and/or “Tutorial for a Top” and PRESTO! Once you’ve read through those tutorials you can find loads of other helpful hints on the site by clicking on the CATEGORIES section, also in the sidebar; scroll down till you find “Ass Fucking”.

Maybe you need to look at alternative sex practices that don’t involve his rump and your rod? Is ass fucking the only thing you guys can think of in terms of sex play and mutual pleasuring? That seems pretty limiting. How about some kinky power play? That sure enough will keep the sexual balance in your relationship. There’s bondage, discipline, milking, jelqing, CBT, edging, fantasy play, watersports, fisting, flogging, massage, rimming, cock sucking, role playing, group sex and vibrators — just to name a few.

How about hiring a pro to attend to your needs? A hot, hunky escort to fuck your partner and do god knows what to you. You see, darling, just because you are 54 and live in Nashville don’t mean your brain’s gone dead…or has it? Like I always say, if there’s a will there’s a way. And hey, maybe that’s a good place to start. Maybe it’s time to check in with your partner to see what new things he’d like to investigate and go from there.

Name: Gilbert
Gender: male
Age: 53
Location: Ohio
I discovered plushie sex long before I knew there were other people in the world who love their stuffed animals as much as I do. At first, I just cuddled and slept with my special plushie, but then I couldn’t help but show my feelings. I wanted to consummate my love for my plushy. The first time I did this I didn’t do anything to my plushie directly. I simply embraced it while I pleasured myself to orgasm. Now my favorite method of expressing my love is to press myself tenderly into my lovers’ plush fur. It’s a truly exquisite sensation!

Lonely are we, Gilbert? YIKES! Say, is your plushie a girl plushie or a boy plushie? Are you sure your plushie, regardless of its gender, likes having you be so…how shall I say this…intimate? And what about the clean up? You say you press yourself tenderly into the plush fur. Good god; it can’t be all that much fun for your plushie tryin to get all your goopy spooge out of its polyester fur, now can it?

And your message isn’t so much of a question as it is a statement, huh Gilbert? Can I assume then that you just wanted to tell the world about gettin your freak on with your beloved plushie? DONE!

For those in my audience who are unable to fathom plushy sex, here is the 411 on this fetish. Some folks, like old Gilbert here, get started down this path by innocently stroking the stuffed animal over their naughty bits. This, I am told, can be the beginning of an intense connection with his/her plushie. Other enthusiasts aren’t satisfied till there is penetration. This is accomplished by modifying the creature at hand by creating what plushies call a ‘strategically-placed hole’ (SPH) on a said plushie. I suppose depending on the gender of the plushie; the ‘strategically-placed hole’ is either a plushie pussy or a plushie asshole, but I digress.

Some fetishists are on the receiving end of plushie sex. That is they create a ‘strategically-placed appendage’ (SPA) on their long-suffering plushie partner and make the little creature fuck them silly(er). SPA, indeed! I mean, god forbid that we call it what it actually is — a freakin’ stuffed animal with a strap-on.

Beyond the human on stuffed animal sex the plushie world also offers plushie on plushie sex too. Of course these are really humans dressed up as plush animals…I mean from head to toe…REALLY! These enthusiasts are generally referred to as furries. Isn’t that adorable?

There are furry sex parties, the like of which I will leave to your fevered imagination, where there’s no end to plushie perversion. I am told that it’s imperative that participants at these parties stay in character. How do you tell the gender of the furry, you might ask? Girl furries often have a bow in their fur. Boy furries, not so often. Ok, I made that part up.

Anyway, the furry outfits are equipped with Velcro held flaps in front and in back. These ‘strategically-placed flaps’ (SPF) give furries access to a fellow furry’s naughty parts. Full-on humping is proceeded by lots of sniffing and nuzzling…you know, exactly like ordinary animals do…only completely different. This is called yiffing. Honestly! Look it up.

I’ve had only two close-up encounters with real live furries. One was a client of mine. Another I met in an online chat room. The chat room connection was so delighted to discover that I was a sexologist that he could hardly contain himself as he revealed to me every gory detail of his furry sex life.

The guy who was my client revealed his furry persuasion in one of his early visits to my office. You see he was having this deep sexual conflict, and as it turned out, it wasn’t that he was dressing up as a big brown bear to get his rocks off.

Here’s how my client related the story. “So here’s the deal,” the guy says. “I’ve been completely straight all my life. A couple of years ago when I discovered I was a furry I went to a few furry sex parties. At one of the parties another male furry began sniffing me and making sexual advances. I would have decked him if I hadn’t been in my bear suit. But because I was being my furry-self his advances were like this complete new turn on. To make a long story short, I got it up the ass but good that night for the very first time.”

You see my client was suddenly conflicted not because he was a furry, don’t ‘cha know. He was conflicted by the discovery that, despite being an exclusively straight macho dude out of costume, he was a freakin’ fag furry in costume. And that, my dear audience, is one of the most bizarre things the good doctor has ever heard.

A curious lot today, don’t cha know. Some folks are simply confused about the concept. Others are just pulling my leg.

Name: agrah
Gender:
Age: 30 ish
Location: michigan
I am curious what the pregnancy rate is for people using anal sex as a means of birth control. While its not my method, (I have an IUD) it is disturbing to me that people think anal sex is fool proof birth control.

HUH? Girl, how’s a chick gonna get pregnant via ass fucking? You explain that to me and I’ll be happy to comment further.

Name: Rocket Man
Gender:
Age: 31
Location: Nashville
Big Dr. Dick, Between busy work schedules, travelling and such, I had not had much time for sex. It was actually about a 5 week span without sex or masturbation. When my wife and I finally got together I was built up big time. I new my response would be quick and my load would likely triple it’s normal oozeage. Being that it had been so long, there was not much foreplay…we just wanted to get down to the hardcore humping. I was sitting on a couch and she climbed on top. On her 3rd downstroke, I blew like a friday afternoon work whistle. She shot off my cock back first into the coffetable, broke it in half and received a few splinters in her ass! Should we replace this piece of furniture, or should I just make her kneel in the floor and rest my legs on her when she’s done sucking me off in the future?

You Nashville folks have all the fun! You get extra points for making me laugh. Perhaps all ya need is sturdier furniture.

PS: don’t be surprised if I steal this: “I blew like a Friday afternoon work whistle.” That’s downright hilarious.

Name: colleen
Gender:
Age: 28
Location: california
I have noticed lately that i am way more horney than normal it is like I can’t ever get enough and the slightes touch gets me going. Also my natural smell from my vagina seems to be extra strong lately and sometimes after my husband and i have sex I have a clear but chunky discharge. I was regulalry with summers eve wash and I have never smelled so strong as I do now. I feel like I am a dog in heat. What is wrong with me?

WHAT’S WRONG WITH YOU? Simply put, you’re 28 and you’re as randy as all get-out, darling. Sounds like you’re pert-near feral. If you were in the wild your super-strong odor would attract males from far and wide; each and every one hoping for his opportunity to satisfy your vixen lusts.

And that “clear but chunky discharge” you’re having after the hubby bones you? Doll, I’d be willing to guess that’s his spooge drippin’ out of your cunt. Ahhh, youth!

Name: lulu
Gender:
Age: 19
Location: dallas
normally my boyfriend wears a condom and if he doesnt he always pulls out, but the other day he cummed inside me and it stung horribly. is this normal??

And what the fuck are you two doin screwin around without always using a condom? You actually trust him to pull out in time…every time? What kind of cockamamie contraceptive strategy is that?

I sure as hell hope you puppies are doubling up on birth control — he, a condom; you, the pill or a diaphragm. Slip-ups happen like clockwork for youngens, like you. That’s why it’s better to be doubly safe than eternally sorry.

Get it done, LuLu! Clearly, your numbskull BF doesn’t use the good sense god gave him, or he’d seal himself in latex before he jumped your bones. Unplanned pregnancies can ruin lives!

Name: Mace
Gender:
Age: 31
Location: Oklahoma City I have an issue with my current girlfriend. She and I are both on the same page with a high sex drive. We both also put a higher priority on satisfying the other before ourselves. My problem is this, I tend to take a longer time to orgasm than my mate. Although she is physically satisfied, she is discouraged at her own sexual prowress because she believes that my climaxing when she does shows that I am as turned on as her. How can I ensure a matching climax, or reassure her that I still think she’s sexy even though I don’t climax?

If it ain’t one thing, it’s another. Are simultaneous orgasms really all that important? Hey, If it happens, it happens. Fine! But personally, I think they’re vastly overrated. Obviously, being turned on and climaxing are not the same thing, so have the GF chill out. Besides, lots of people find it a huge turn on to watch their partner cum. And one can’t hardly enjoy the show if one is busy producing his or her own display, right?

Mark my words, the added pressure to cum simultaneously will only induce a serious case of performance anxiety in one or the both of you. And that will sure-as-shootin’ throw a monkey wrench into the sweet thing you guys got goin on.

Name: sarah
Gender:
Age: 18
Location: detroit
why do anal sex hurt so bad what can i do to stop the pain

Nope, it doesn’t always hurt so bad. Sometimes it hurts so good.

Chances are the guy who’s pluggin you doesn’t know what the fuck he’s doin. Just because he has a cock and you have a bunghole don’t make you experts butt pirates.

From the sublime to the ridiculous, my inbox is a catch all. Kinda like the grease trap in your kitchen drain. Wading through the detritus can often be injurious to my health. But wade I must. So onward we go.

Name: anonras
Gender:
Age: 47
Location: Northridge CA
I’ve heard a lot about checking your balls for possible problems — but none ever say what lumps you have naturally. At the low point of my testacies I feel a lump (I would explain it as an area that would feel more or less like a cracked egg, you have that part that is globulous and is string-tethered to the yoke. Is that exactly what’s happening? Should you feel any pain if you squeeze it — especially trying to figure out if it is a lump or not?

Honey, I’m clever as all-get out about lots of things, but the lump on your balls ain’t one of those things. I’m not a medical doctor; I don’t even play one here on the internets. And I can assure you, no reputable doctor anywhere would hazard a guess about what you present without first seeing you in person. That’s just good medicine.

That being said, I applaud you taking note of your balls in an inquisitive sort of way. Good for you! But you should also have at least a rudimentary understanding of your testicular anatomy. So that when you do your self-exam, you can have some sense about what it is you are examining. To this purpose, I offer the diagram to the right. Is there anything in the diagram that looks even remotely like what you are feeling in your ballsack?

Finally, if you have a concern about what you think may be an abnormality, isn’t it high time for you to high tail it to a doctor for a look-see?

Good luck

Name: Dorian
Gender:
Age: 18
Location: NYC
Is there any difference in Penis size between races?

Seriously? You need to get out more, darlin!
You becha there a difference in cock size between the races. While, within each racial group there is a natural diversity of size, from tiny to gargantuan. There’s no getting around the fact that there are more gargantuan johnsons in some racial groups then other. At the risk of perpetuating a stereotype, compare some fine black dick to some sweet Chinese cock.

Good luck

Name: Kent I B Pinker
Gender:
Age: 32
Location: New Zealand
I am curious about anal bleaching. In part just for the sheer vanity of it, but also as a surprise and kinky turn on for my partner. I have done some research online but I am scared after reading some of the horror stories. Any advice?

Kent I B Pinker? I love it! You get the award for “Most Clever Pseudonym of the Year! Congratulations!

If you’re curious about anal bleaching — and yes, there is such a thing — you have way too much time on your hands. Anal bleaching is just the latest in a string of truly disturbing cosmetic trends sweeping the “More Money Than Brains” crowd. WTF, folks? If your vanity extends to the hue of your rosebud, you’re just too goddamn vain, in my humble opinion!

This all started in the adult industry, don’t ‘cha know. I guess some folks figured they weren’t quite ready for their close-up. Being part of that industry myself, I know how unforgiving hot lights and hi-def can be. However, I still can’t condone such a dangerous and reckless practice.

You are right to be scared off by the horror stories of bleachings gone bad, Kent. So I suggest, unless your hole is makin’ you money, you forego even contemplating the procedure.

Good luck

Name: William
Gender:
Age: 67
Location: Connecticut
Is there such a thing as a being a homosexual watcher only? Getting an erection but not wanting to perform?

All sexual orientation is on a continuum. See the Kinsey Scale to the right. The dean of American sex research, Alfred Kinsey, his associate, Wardell Pomeroy, and others developed this scale as a way of classifying a person’s sexuality in terms of both behavior and fantasy. These pioneering sexologists also found that an individual may be reassigned a position on this scale, at different periods in his/her life. It’s conceivable that one could go from 0 to 6 in a lifetime, or just a summer on Fire Island. This seven-point scale comes close to showing the many gradations that actually exist in human sexual expression.

To your specific question, William… Yes, some one could be a Kinsey “6” in terms of his fantasy and desire, but be a Kinsey “0” in terms of behaviors.

We’re amazing creatures, huh?

Good Luck

Name: michelle
Gender:
Age: 22
Location: canada
tips to help when the man your sleeping with has a small penis

Tips? …no pun intended, I hope.

Ok, here goes — Tip #1, grin and bear it. Tip #2, find a guy with more pork. Tip #3, get a dildo. Tip #4, find a sexual position, like doggie style, that will make the most of every little bit of pecker the poor guy’s got. Tip #5, remember it ain’t always da meat, but it is always da motion.

Good luck

Name: Drew
Gender:
Age: 43
Location: Philadelphia
I am looking forward to my first man-on-man sex for the first time with a hookup in the near future. Question: What type of “preparation” do I need for my first anal sex? Also, should I use a condom with giving/getting oral sex? Thanks.

You’re in luck, newbee butt-pirate! Dr Dick has written (postings) and spoken (podcasts) extensively about the joys of ass fucking. Check out the CATEGORIES section on the left side of the site. Look for anything with the word “ass” in it. We don’t mince words around here. Or you can simply search for Liberating The B.O.B. Within. That’ll get ya started.

As to your concern about condom-covered dick for blowjobs; I don’t see a pressing reason for such. That’s not to say there’s no reason, just not a pressing one. I am of the mind that we ought to know something about the dick we’re sucking. Does it look healthy? Do you know where it’s been before it was in your mouth? How’s our oral health and hygiene? Will there be an exchange of bodily fluids? If you have questions about any of these things, maybe you need to postpone the cocksucking.

Good luck

Name: william
Gender:
Age: 19
Location: Wisconsin
In cock size, is 4 1/2 to small. Why is it so small and is there a way to fix it.

Jeez, ya mean 4.5” erect? Yeah, that’s kinda on the “How Adorable” end of the size spectrum. It’s not quite, “OMG, How Pathetic”, nor is it “Yikes, You’ll Put an Eye Out With That” either.

Why is it so small? Sheesh, beats me. Maybe when the angles were handing out meat, you thought they said “feet” and asked for petite.

Is there a way to fix it? Are you suggesting it doesn’t work? Or are you just a size queen? While you’re trying to figure that out, why not take a look at: Much Ado About Very Little.